European Journal of Organic Chemistry

Cover image for Vol. 2015 Issue 13

Early View (Online Version of Record published before inclusion in an issue)

Editor: Haymo Ross, Deputy Editor: Susan Wilkinson

Impact Factor: 3.154

ISI Journal Citation Reports © Ranking: 2013: 14/58 (Chemistry Organic)

Online ISSN: 1099-0690

Associated Title(s): Advanced Synthesis & Catalysis, Asian Journal of Organic Chemistry

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  1. 1 - 75
  1. Full Papers

    1. N-Acyliminium Ions

      Synthesis of Substituted γ- and δ-Lactams through Mannich-Type Reactions of Solid-Supported N-Acyliminium Ions

      Vitaly V. Komnatnyy, Kennedy M. Taveras, Nitin S. Nandurkar, Sebastian T. Le Quement, Michael Givskov and Thomas E. Nielsen

      Article first published online: 27 APR 2015 | DOI: 10.1002/ejoc.201500054

      Thumbnail image of graphical abstract

      A new and efficient method for the solid-phase synthesis of diversely substituted γ- and δ-lactams through Mannich-type reactions of cyclic N-acyliminium ions is presented. A wide range of external aromatic and heteroaromatic carbon nucleophiles could be successfully used in the sequence.

    2. Stille Cross-Coupling

      Stille Cross-Coupling for the Functionalization of the Imidazole Backbone: Revisit, Improvement, and Applications of the Method

      Alexander H. Sandtorv, Karl Wilhelm Törnroos and Hans-René Bjørsvik

      Article first published online: 27 APR 2015 | DOI: 10.1002/ejoc.201500328

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      Stille cross-coupling methodology for the functionalization of the imidazole backbone was realized and investigated. Mono-coupling on the imidazole backbone was successfully conducted aided by a double catalytic cycle comprising CuI and Pd. Different auxiliary groups installed on the N-1 ring atom of the imidazole mediates either mono-coupling (Tos) or bis-coupling (DMAS) in excellent yields.

    3. Oxygen Heterocycles

      Unusual Reactivity of Aryl Aldehydes with Triethyl Phosphite and Zinc Bromide: A Facile Preparation of Epoxides, Benzisoxazoles, and α-Hydroxy Phosphonate Esters

      Potharaju Raju, Ganesan Gobi Rajeshwaran, Meganathan Nandakumar and Arasambattu K. Mohanakrishnan

      Article first published online: 24 APR 2015 | DOI: 10.1002/ejoc.201500332

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      A (EtO)3P–ZnBr2-mediated deoxygenation reaction of 2-nitrobenzaldehydes was developed for the facile preparation of trans-epoxides. When sterically hindered 2-nitrobenzaldehydes were treated with triethyl phosphite and ZnBr2, benzisoxazoles were formed as the sole product. Electron-rich and moderately electron-deficient aryl aldehydes gave α-hydroxy phosphonate esters under identical conditions.

    4. Benzotriazolodiazepinones

      Solid-Phase Synthesis of Trisubstituted Benzo[f][1,2,3]triazolo[1,5-a][1,4]diazepin-6(5H)-ones and Their Sulfonyl Analogues under Mild Reaction Conditions

      Veronika Fülöpová, Petr Funk, Igor Popa, Claire McMaster and Miroslav Soural

      Article first published online: 24 APR 2015 | DOI: 10.1002/ejoc.201500314

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      The solid-phase synthesis of 4H-benzo[f][1,2,3]triazolo[1,5-a][1,4]diazepin-6(5H)-ones and 4,5-dihydrobenzo[f][1,2,3]triazolo[5,1-d][1,2,5]thiadiazepine 6,6-dioxides under mild and catalyst-free conditions has been developed. The target compounds were obtained in excellent crude purities and very good overall yields.

    5. [3+3] Annulation

      Sc(OTf)3-Catalysed [3+3] Annulation of Cyclopropane 1,1-Diesters with Mercaptoacetaldehyde: A Facile Strategy for the Synthesis of Tetrahydrothiopyranols

      Hua-Peng Wang, Huan-Huan Zhang, Xiu-Qin Hu, Peng-Fei Xu and Yong-Chun Luo

      Article first published online: 23 APR 2015 | DOI: 10.1002/ejoc.201500282

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      A catalytic [3+3] annulation of cyclopropane 1,1-diesters with in-situ-generated mercaptoacetaldehyde for the synthesis of polyfunctionalized tetrahydrothiopyran derivatives has been developed. A ring-opening/aldol cascade reaction catalysed by Sc(OTf)3 (10 mol-%) gave a series of tetrahydrothiopyranols in good yields. Simple derivatization of the products gave some useful compounds.

  2. Short Communications

    1. Natural Product Synthesis

      A Flexible Route to Indole Scaffolds – Formal Synthesis of (±)-Mersicarpine

      Magnus Pfaffenbach and Tanja Gaich

      Article first published online: 23 APR 2015 | DOI: 10.1002/ejoc.201500309

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      A concise, formal synthesis of mersicarpine in eight isolated steps was developed with an overall yield of 6 % from commercially inexpensive starting material. The route is operationally simple, efficient, and further allows the construction of two completely different polycyclic alkaloid skeletons from a common intermediate.

  3. Full Papers

    1. Cross-Coupling

      Suzuki–Miyaura Reactions of Halospirooxindole Derivatives

      Abderrahman El Bouakher, Hassan Allouchi, Isabelle Abrunhosa-Thomas, Yves Troin and Gérald Guillaumet

      Article first published online: 23 APR 2015 | DOI: 10.1002/ejoc.201500268

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      A library of 5- or 5′-monosubstituted and 5,5′-disubstituted 1′-pentyl-2H-spiro[furo[2,3-b]pyridine-3,3′-indolin]-2′ones has been efficiently prepared through Suzuki–Miyaura reactions conducted under microwave conditions.

    2. β-Hydroxy Nitrile Synthesis

      α-Alkyl-α-aryl (Trimethyltin) Nitriles: Versatile Nucleophilic Intermediates in Aldol-Like Reactions

      Wenling Qin, Sha Long, Alessandro Bongini and Mauro Panunzio

      Article first published online: 22 APR 2015 | DOI: 10.1002/ejoc.201500299

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      α-Alkyl-α-aryl (trimethyltin) nitriles react spontaneously with aldehydes and ketones in THF/toluene to give β-hydroxy nitriles. A possible intermediate trimethyltin-ketene imine is invoked as reactive species. DFT calculations support this hypothesis. The new tin reagent may be considered an alternative option to the silylketene imines.

    3. Cross-Coupling Reactions

      Development of Unimolecular Tetrakis(piperidin-4-ol) as a Ligand for Suzuki–Miyaura Cross-Coupling Reactions: Synthesis of Incrustoporin and Preclamol

      Jothi L. Nallasivam and Rodney A. Fernandes

      Article first published online: 22 APR 2015 | DOI: 10.1002/ejoc.201500353

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      A domino aza-Cope/aza-Prins cascade enabled the synthesis of a new class of 4-hydroxypiperidine-appended mono-, bis-, tris-, and tetrakis-unimolecular compounds that served as efficient ligands to catalyze Suzuki–Miyaura cross-coupling reactions under aerobic conditions. Various biaryls, terphenyls, and heterocyclic biphenyls were obtained in good to excellent yields.

    4. Trifluoromethylthiolation

      Copper(I)-Mediated Direct Trifluoromethylthiolation of Allylic Halides with Elemental Sulfur and (Trifluoromethyl)trimethylsilane

      Jue Li, Peiqiang Wang, Fei-Fei Xie, Xi-Gang Yang, Xiao-Nan Song, Wei-Dong Chen, Jiangmeng Ren and Bu-Bing Zeng

      Article first published online: 22 APR 2015 | DOI: 10.1002/ejoc.201500384

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      A novel, mild and efficient approach for the synthesis of allylic trifluoromethyl thioethers by using DMF as solvent, CuSCN as copper salt, dry KF as base, S8 and TMSCF3 as trifluoromethanethiol source at 45 °C was developed. The obvious advantages of this method are that the reaction proceeds smoothly under mild and ligand-free conditions, with good yields, and with a wide range of substrates as well as inexpensive and non-toxic reagents.

  4. Short Communications

    1. Carbonylation

      Facile, One-Step Synthesis of 5-Substituted Thieno[3,4-c]pyrrole-4,6-dione by Palladium-Catalyzed Carbonylative Amidation

      Shinichiro Fuse, Ryota Takahashi and Takashi Takahashi

      Article first published online: 22 APR 2015 | DOI: 10.1002/ejoc.201500273

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      A facile, one-step synthesis of 5-substituted thieno[3,4-c]pyrrole-4,6-diones (TPDs) by a palladium-catalyzed carbonylative amidation of commercially available dibromoaryl compounds under mild conditions was achieved. In addition, the developed method was applied to the syntheses of pyridinopyrroledione (PPD) and pyrroloisoindoletetraone (PIT).

  5. Full Papers

    1. Anti-Inflammatory Macrolactones

      Synthetic Approaches to Anti-Inflammatory Macrolactones of the Oxacyclododecindione Type

      Johannes Tauber, Kristina Rudolph, Markus Rohr, Gerhard Erkel and Till Opatz

      Article first published online: 21 APR 2015 | DOI: 10.1002/ejoc.201500275

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      The oxacyclododecindione-type macrolactones are known for their potent anti-inflammatory activity. A bioactive analogue of the recently described 14-deoxyoxacyclododecindione was synthesized by an RCM/hydrogenation/dehydrogenation sequence. Various other approaches such as carbonylative cross-coupling or intramolecular hydroacylation failed to produce the 12-membered lactone skeleton.

  6. Short Communications

    1. Fluorescent Boron Complexes

      Synthesis, Post-Modification and Fluorescence Properties of Boron Diketonate Complexes

      Samuel Guieu, Joana Pinto, Vera L. M. Silva, João Rocha and Artur M. S. Silva

      Article first published online: 21 APR 2015 | DOI: 10.1002/ejoc.201500318

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      A family of fluorescent dyes based on a boron diketonate core with extended conjugation has been prepared by a three-step strategy. The complexes are brightly emissive in both solution and the solid state, with large Stokes' shifts.

    2. Triazole Synthesis

      A Facile One-Pot Metal-Free Synthesis of 1,4-Disubstituted 1,2,3-Triazoles

      Qianfa Jia, Gongming Yang, Lei Chen, Zhiyun Du, Jia Wei, Yanqiong Zhong and Jian Wang

      Article first published online: 21 APR 2015 | DOI: 10.1002/ejoc.201500360

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      A one-pot synthesis of 1,4-disubstituted 1,2,3-triazoles by 1,3-dipolar cycloaddition reaction has been developed. This strategy provides a rapid and efficiency way to construct 1,4-disubstitued 1,2,3-triazoldes in good to excellent yields and high levels of regioselectivity (r.r. = ratio of regioisomers).

  7. Full Papers

    1. Liquid Crystals

      Synthesis of Functionalized Organoselenium Materials: Selenides and Diselenides Containing Cholesterol

      Tiago E. Frizon, Jamal Rafique, Sumbal Saba, Ivan H. Bechtold, Hugo Gallardo and Antonio L. Braga

      Article first published online: 21 APR 2015 | DOI: 10.1002/ejoc.201500124

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      A new series of selenide and diselenide liquid crystals containing cholesterol were synthesized and characterized. Most of the materials presented good thermal stability with SmC* and SmA* phases over a wide temperature range. The prepared diselenides also have potential biological applications, and they showed good antioxidant properties.

    2. Multicomponent Reactions

      Copper(I)-Catalyzed A3-Coupling Based Reaction of Alkynes, Aldehydes, and Amines: An Efficient Approach to 2,5-Polysubstituted Dihydrofurans and 2,5-Disubstituted Furans

      Wu Fan and Shengming Ma

      Article first published online: 21 APR 2015 | DOI: 10.1002/ejoc.201500209

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      An efficient and practical A3-coupling based reaction that gives a variety of 2,5-polysubstituted dihydrofurans has been developed. The starting materials are commercially available, and the reaction conditions are mild. In addition, 2,5-disubstituted furans can be prepared by treating the dihydrofuran derivatives with CH3I and base in a two-step reaction sequence.

    3. Synthetic Methods

      α-Carbonylimine to α-Carbonylamide: An Efficient Oxidative Amidation Approach

      Anil K. Padala, Nagaraju Mupparapu, Deepika Singh, Ram A. Vishwakarma and Qazi Naveed Ahmed

      Article first published online: 21 APR 2015 | DOI: 10.1002/ejoc.201500251

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      An efficient oxidative amidation reaction between 2-oxoaldehyde and weak nucleophilic amines (anilines, benzamides, and sulfonamides) is reported. Mechanistic studies show that α-carbonylimine (–CO–C=N–) based compounds are a central feature of the reaction. It was found that an adjacent CO moiety enhances the electrophilicity of the C=N system, which favors attack of oxidant (TBHP or SeO2).

    4. Anti-Michael Addition

      Hydrogen Bond Controlled Anti-Aza-Michael Addition: Diastereoselective Synthesis of Cyclobutene-Containing Amino Acid Derivatives

      David Tejedor, Gabriela Méndez-Abt, Javier González-Platas, Israel Fernández and Fernando García-Tellado

      Article first published online: 20 APR 2015 | DOI: 10.1002/ejoc.201500269

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      The H-bond makes the difference. The stereochemical outcome of the nucleophilic addition of secondary amines to a fully substituted cyclobutane platform is governed by an NH···O=C interaction between the incoming amine and benzoate leaving group. This interaction directs the addition to the same face as that of the leaving group to form the most kinetically accessible amino acid derivative.

  8. Short Communications

    1. Direct C–H Arylations

      Palladium-Catalyzed Direct C–H Arylation of Dicyanobenzenes

      Netta E. Ihanainen, Esa T. T. Kumpulainen and Ari M. P. Koskinen

      Article first published online: 20 APR 2015 | DOI: 10.1002/ejoc.201500288

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      A direct palladium-catalyzed C–H arylation method to synthesize biaryls from dicyanobenzenes and other electron-deficient benzonitriles has been developed. A variety of functional groups are tolerated, and yields up to 83 % can be obtained.

    2. Calixradialenes

      Preparation and Crystal Structure of the 1,3-alternate Atropisomer of a Calix[4]radialene

      Norbert Itzhak and Silvio E. Biali

      Article first published online: 20 APR 2015 | DOI: 10.1002/ejoc.201500319

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      A rigid calix[4]radialene was prepared and structurally characterized. The crystal structure determination corroborates the presence of the four exocyclic double bonds and the 1,3-alternate arrangement of the aryl rings.

  9. Full Papers

    1. Regioselective Coupling

      Synthesis of Diiodinated Biphenyls and Iodinated meta-Terphenyls by Regioselective Suzuki–Miyaura Cross-Coupling Reactions of 5-Substituted 1,2,3-Triiodobenzenes

      Raed M. Al-Zoubi, Walid K. Al-Jammal, Mohammad Y. El-Khateeb and Robert McDonald

      Article first published online: 17 APR 2015 | DOI: 10.1002/ejoc.201500263

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      A facile and efficient one-step method is reported for the synthesis of 2,3-diiodinated biphenyl and iodinated meta-terphenyl derivatives by employing Suzuki–Miyaura cross-coupling reactions of 5-substituted 1,2,3-triiodobenzenes. This reaction is general in scope, scalable, and highly regioselective.

  10. Microreviews

    1. Fluorination of Pyrazoles

      Selective Incorporation of Fluorine in Pyrazoles

      Joseph C. Sloop, Cory Holder and Maged Henary

      Article first published online: 17 APR 2015 | DOI: 10.1002/ejoc.201500258

      Thumbnail image of graphical abstract

      Methods for the assembly of fluorinated pyrazoles and the selective incorporation of fluorine and fluorine-containing moieties into the pyrazolic architecture are reviewed. Nucleophilic, electrophilic, radical and metal-mediated fluorination processes are considered. Reagents, precursors and reaction conditions found most suitable in processes leading to fluorinated pyrazoles are examined in detail.

  11. Full Papers

    1. Conjugate Addition

      Synthesis of Boron- and Silicon-Containing Amino Acids through Copper-Catalysed Conjugate Additions to Dehydroalanine Derivatives

      Francesca Bartoccini, Silvia Bartolucci, Simone Lucarini and Giovanni Piersanti

      Article first published online: 17 APR 2015 | DOI: 10.1002/ejoc.201500362

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      Copper mediated β-boration and β-silylation of a variety of dehydroalanine and dehydropeptide compounds gives ready access to orthogonally N- and C-protected boron- and silicon-containing amino acids and small peptides.

    2. Transfer Hydrogenation

      Highly Enantioselective SPINOL-Derived Phosphoric Acid Catalyzed Transfer Hydrogenation of Diverse C=N-Containing Heterocycles

      Yiliang Zhang, Rong Zhao, Robert Li-Yuan Bao and Lei Shi

      Article first published online: 17 APR 2015 | DOI: 10.1002/ejoc.201500330

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      Chiral SPINOL-derived phosphoric acids are highly enantioselective catalysts for the asymmetric transfer hydrogenation of diversely substituted C=N-containing heterocyclic compounds (SPA = SPINOL-derived phosphoric acids). The method provides straightforward access to various optically active tetrahydroquinolines and dihydro-2H-1,4-benzothiazines in high yields with excellent enantioselectivities.

    3. H–D Exchange

      A Simple and Cost-Effective Method for the Regioselective Deuteration of Phenols

      Miao Zhan, Ruixue Xu, Ye Tian, Hongxia Jiang, Lifeng Zhao, Yongmei Xie and Yuanwei Chen

      Article first published online: 17 APR 2015 | DOI: 10.1002/ejoc.201500192

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      An efficient method for the synthesis of regioselectively deuterated phenols under microwave irradiation was developed. The method also allowed the deuteration of complex pharmaceutically interesting substrates.

    4. Selenium-Mediated Epoxidation

      Terpenyl Selenides: Synthesis and Application in Asymmetric Epoxidation

      Anna Banach, Jacek Ścianowski, Magdalena Uzarewicz-Baig and Andrzej Wojtczak

      Article first published online: 17 APR 2015 | DOI: 10.1002/ejoc.201500211

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      Selenium-mediated asymmetric epoxidation through the use isoselenocineole, and methyl terpenyl, phenyl terpenyl, and diterpenyl selenides is presented. The influence of reaction conditions, counteranion, and purity of selenonium salt on the reaction of asymmetric epoxidation is described.

    5. Catalytic Olefinations

      Phospholane-Catalyzed Wittig Reaction

      Thomas Werner, Marcel Hoffmann and Sunetra Deshmukh

      Article first published online: 17 APR 2015 | DOI: 10.1002/ejoc.201500243

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      A suitable and potentially tunable catalyst for the catalytic Wittig reaction is presented. The scope and limitations of this catalyst were evaluated, and over 20 examples are reported. Moreover, efforts to utilize chiral analogues of the catalyst for the desymmetrization of a pro-chiral diketone are reported.

    6. Organic Synthesis

      Synthesis of Enantiopure 1,5-Enynes and 1,5-Diynes with Propargylic Quaternary Centers

      Ignacio Pérez, Francisco Yuste, Rubén Sánchez-Obregón, Rubén A. Toscano, José Alemán, Leyre Marzo, Ana M. Martín Castro, Inés Alonso and José Luis García Ruano

      Article first published online: 17 APR 2015 | DOI: 10.1002/ejoc.201500004

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      Diastereoselective quaternization of o-sulfinylbenzyl-methylpropargylic carbanions has been achieved with allylic, propargylic, and benzylic halides. The stereoselectivity is efficiently controlled by the sulfinyl group, acting as a remote chiral auxiliary. This method provides access to enantiopure 1,5-enynes, 1,5-diynes, and 4-arylalkynes bearing quaternary propargylic centers.

  12. Short Communications

    1. 1,3-Selenazoles

      One-Pot Synthesis of 2-Amino-1,3-selenazole via an Intermediary Amidinoselenourea

      Alok Ranjan, Ragini Yerande, Mahantesh Jadhav, Swapnil G. Yerande and Dattatraya H. Dethe

      Article first published online: 17 APR 2015 | DOI: 10.1002/ejoc.201500168

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      An efficient method for the synthesis of 2-amino-1,3-selenazole by a sequential one-pot multicomponent reaction between isoselenocyanate and N,N-diethyl-amidine has been developed. It represents a step-economical way to construct a range of 2-amino-1,3-selenazole derivatives in 65–89 % yields. The structure of the trisubstituted selenazole formed was unambiguously established by X-ray crystallography.

  13. Full Papers

    1. Natural Products

      Collective Synthesis of Natural Products Sharing the Dihydro-γ-Ionone Core

      Alexis Castillo, Lucia Silva, David Briones, José F. Quílez del Moral and Alejandro F. Barrero

      Article first published online: 16 APR 2015 | DOI: 10.1002/ejoc.201500208

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      The expedient enantioselective synthesis of several natural products from a common precursor, (+)-3,4-dihydro-γ-ionone, is described. The production of this natural compound in multigram scale from the extract Bellardia trixago is the basis of this approach.

    2. Pd-Catalyzed α-Arylation

      Umpolung Pd-Catalyzed α-Arylation Reactions in Natural Product Synthesis: Syntheses of (+)-Xestodecalactone A, (–)-Curvularin, (+)-12-Oxocurvularin and (–)-Citreofuran

      Dripta De Joarder and Michael P. Jennings

      Article first published online: 14 APR 2015 | DOI: 10.1002/ejoc.201500287

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      The total syntheses of (+)-xestodecalactone A, (–)-curvularin, and formal syntheses of (+)-12-oxocurvularin and (–)-citreofuran have been accomplished by utilizing a unified strategy of an umpolung Pd-catalyzed α-arylation of complex α-bromo esters and boronic acids under mild reaction conditions.

  14. Short Communications

    1. Pt(II)-Functionalized Crownophanes

      A Dinuclear (bpy)PtII-Decorated Crownophane

      Ilona Stengel, Günther Götz, Matthias Weil and Peter Bäuerle

      Article first published online: 14 APR 2015 | DOI: 10.1002/ejoc.201500213

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      A [13.3.3](1,2,4)crownophane was designed and synthesized as a functional bridging ligand for a dinuclear PtII complex. The structure and the breathing function of the crownophane moiety were investigated in detail. Furthermore, the photophysics of the final dinuclear PtII compound were studied.

  15. Full Papers

    1. Sulfoximines

      The Synthesis of Chiral Benzothiazine and Thiazinoquinoline Derivatives

      Long Wang, Daniel L. Priebbenow, Xiao Yun Chen, Fang-Fang Pan and Carsten Bolm

      Article first published online: 10 APR 2015 | DOI: 10.1002/ejoc.201500250

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      2,1-Benzothiazine and thiazinoquinoline derivatives were prepared by using an 8-amino-2,1-benzothiazine as a key intermediate. These compounds are rigid variants of a highly enantioselective sulfoximine ligand that was previously used for copper-catalyzed Mukaiyama-type aldol reactions. Our derivatives actively catalyzed the same C–C bond formation but with much lower enantioselectivities.

    2. Synthetic Methods

      Regioisomerically Pure 1,7-Dibromo-Substituted Perylene Bisimide Dyes: Efficient Synthesis, Separation, and Characterization

      Jiajun Ma, Leicheng Yin, Gang Zou and Qijin Zhang

      Article first published online: 9 APR 2015 | DOI: 10.1002/ejoc.201500206

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      1,7-Dibromo-substituted perylene bisimides have been isolated from regioisomeric mixtures by column chromatography in yields of at least 60 %. The 1,7-disubstituted intermediates can provide a convenient and efficient approach to novel perylene bisimide derivatives.

    3. Modular Cyclization

      Tandem Arylation/Friedel–Crafts Reactions of o-Acylanilines with Diaryliodonium Salts: A Modular Synthesis of Acridine Derivatives

      Xinlong Pang, Zhenbang Lou, Ming Li, Lirong Wen and Chao Chen

      Article first published online: 9 APR 2015 | DOI: 10.1002/ejoc.201500161

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      A tandem cyclization reaction to produce acridine derivatives was realized with o-acylanilines and diaryliodonium salts under Cu-catalyzed or metal-free reaction conditions at elevated temperature.

    4. Organocatalysis

      Highly Enantioselective Synthesis of Chiral Pyranonaphthoquinone-Fused Spirooxindoles through Organocatalytic Three-Component Cascade Reactions

      Hong-Wu Zhao, Bo Li, Ting Tian, Wei Meng, Zhao Yang, Xiu-Qing Song, Xiao-Qin Chen and Hai-Liang Pang

      Article first published online: 8 APR 2015 | DOI: 10.1002/ejoc.201500152

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      In the presence of cinchona-thiourea catalyst C1, the developed organocascade three-component reaction of isatins, malononitrile, and 2-hydroxynaphthalene-1,4-diones readily proceeded to furnish desired chiral pyranonaphthoquinone-fused spirooxindoles in excellent chemical yields and high enantioselectivities (up to 99 % yield and 97 % ee).

  16. Short Communications

    1. Intramolecular Heck Reaction

      Synthesis of Rigid Analogues of Flavone by Intramolecular Heck Reaction

      Chuanwei Hou, Hao Chen, Xing Xu, Fangxia Zhu, Lei Guo, Min Jiang, Chunhao Yang and Lianfu Deng

      Article first published online: 8 APR 2015 | DOI: 10.1002/ejoc.201500180

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      As the title reaction shows, rigid analogues of flavone were synthesized by an intramolecular Heck reaction from 3-(2-bromobenzyl)-4H-chromen-4-ones, which could be prepared easily in two steps. Most compounds were obtained with moderate to good yields.

    2. Iron Catalysis

      Iron-Catalyzed α-Methylenation of Ketones with N,N-Dimethylacetamide: An Approach for α,β-Unsaturated Carbonyl Compounds

      Yi-Ming Li, Shao-Jie Lou, Qin-Hua Zhou, Lian-Wen Zhu, Long-Feng Zhu and Lei Li

      Article first published online: 8 APR 2015 | DOI: 10.1002/ejoc.201500189

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      A general and facile iron-catalyzed α-methylenation of carbonyl compounds by using N-methyl amides as the one-carbon source was developed. Various carbonyl compounds (aryl- or alkyl-substituted, enones, 1,3-dicarbonyl compounds) were well tolerated to furnish the corresponding α,β-unsaturated carbonyl compounds in the presence of an iron catalyst, peroxides, and N-methyl amides under aerobic conditions.

    3. Fluorinated Amino Acids

      Flow Synthesis of Fluorinated α-Amino Acids

      Stella Vukelić, Dmitry B. Ushakov, Kerry Gilmore, Beate Koksch and Peter H. Seeberger

      Article first published online: 8 APR 2015 | DOI: 10.1002/ejoc.201500300

      Thumbnail image of graphical abstract

      An efficient, semi-continuous, and protecting-group-free method for the synthesis of fluorinated α-amino acids from the corresponding amines has been developed. A low temperature photooxidative cyanation of benzylic and aliphatic amines provided α-amino nitriles with varying fluorination patterns. These unstable intermediates were trapped with an acid-mediated hydrolysis with good overall yields.

  17. Full Papers

    1. Gold(I) Catalysis

      Gold-Catalysed Synthesis of Exocyclic Vinylogous Amides and β-Amino Ketones: A Detailed Study on the 5-exo/6-endo-dig Selectivity, Methodology and Scope

      Dina Scarpi, Stefano Begliomini, Cristina Prandi, Alberto Oppedisano, Annamaria Deagostino, Enrique Gómez-Bengoa, Béla Fiser and Ernesto G. Occhiato

      Article first published online: 8 APR 2015 | DOI: 10.1002/ejoc.201500205

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      The gold(I)-catalysed reaction of N-alkoxycarbonyl-protected 6-alkynyl-3,4-dihydro-2H-pyridines gives synthetically useful vinylogous amides (β-enaminones). The 6-endo-dig approach is exclusive with substituted alkynes, whereas with terminal alkynes the 5-exo-dig cyclization prevails. The extension of the approach to β-amino ketones is also described.

    2. Salicyldialdehyde Synthesis

      Synthesis of para-Aryl-Substituted Salicyldialdehydes

      Dennis Reinhard, Ludger Schöttner, Victor Brosius, Frank Rominger and Michael Mastalerz

      Article first published online: 8 APR 2015 | DOI: 10.1002/ejoc.201500228

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      Two complementary synthetic routes to 4-arylsalicyldialdehydes are elaborated and compared for various substrates. Unexpected byproducts as well as preliminary results on cage formation are also discussed.

  18. Short Communications

    1. Asymmetric Catalysis

      4,8-Disubstituted Bicyclo[3.3.1]nona-2,6-dienes as Chiral Ligands for Rh-Catalyzed Asymmetric 1,4-Addition Reactions

      Renaldas Rimkus, Marius Jurgelėnas and Sigitas Stončius

      Article first published online: 8 APR 2015 | DOI: 10.1002/ejoc.201500202

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      Chiral C2-symmetric 4,8-endo,endo-disubstituted bicyclo[3.3.1]nona-2,6-diene ligands were synthesized from easily available bicyclo[3.3.1]nonane-2,6-dione and utilized in the asymmetric 1,4-addition reaction of arylboronic acids to cyclic enones. The catalyst prepared in situ from ligand 4b and [RhCl(C2H4)2]2 exhibited excellent catalytic activity and high enantioselectivity (up to 96 % ee) under mild reaction conditions with high atom efficiency.

  19. Full Papers

    1. Total Synthesis

      Total Synthesis of the Putative Structure of Deoxypumiliotoxin 193H by an Ireland–Claisen Rearrangement

      Gints Smits and Ronalds Zemribo

      Article first published online: 7 APR 2015 | DOI: 10.1002/ejoc.201500063

      Thumbnail image of graphical abstract

      A stereoselective total synthesis of 8-deoxypumiliotoxin 193H is described. The concise total synthesis features the use of readily available starting materials, namely, natural amino acids and the Ireland–Claisen rearrangement as the key stereochemistry controlling step.

    2. Heterocyclic Chemistry

      Tandem Prins Cyclization for the Stereoselective Synthesis of the 4,5-Diaryl-hexahydropyrano[3,4-c]chromene Skeleton of Calyxins I and J

      Basi V. Subba Reddy, Mittapalli Ramana Reddy, Sama Gopal Reddy, Balasubramanyan Sridhar and Singarapu Kiran Kumar

      Article first published online: 7 APR 2015 | DOI: 10.1002/ejoc.201500117

      Thumbnail image of graphical abstract

      A Prins-type bicyclization strategy for the stereoselective synthesis of trans-fused hexahydropyrano[3,4-c]chromene derivatives in good to excellent yields is reported.

    3. Crystal Engineering

      Connecting Electron-Deficient and Electron-Rich Aromatics to Support Intermolecular Interactions in Crystals

      Markus Albrecht, Hai Yi, Fangfang Pan, Arto Valkonen and Kari Rissanen

      Article first published online: 7 APR 2015 | DOI: 10.1002/ejoc.201500175

      Thumbnail image of graphical abstract

      Polar effects introduced by a combination of electron-poor and electron-rich aromatics within one compound control the packing of the crystal based on intermolecular hydrogen bonding, aryl···aryl interactions, and even uncommon non-classical CF···HC hydrogen bonding.

    4. β-Oxo Amides

      Silver(I)-Catalyzed Tandem Approach to β-Oxo Amides

      Jaya Kishore Vandavasi, Cheng-Tien Hsiao, Wan-Ping Hu, Siva Senthil Kumar Boominathan and Jeh-Jeng Wang

      Article first published online: 7 APR 2015 | DOI: 10.1002/ejoc.201500224

      Thumbnail image of graphical abstract

      A new, catalytic approach to the synthesis of β-oxo amides from β-oxo esters with a broad substrate scope in good to excellent yields was developed. In situ NMR spectroscopy and crossover experiments confirmed the reaction mechanism.

    5. Tandem Reactions

      Synthesis of Multisubstituted Dihydroquinoxaline Derivatives by Tandem N-Alkylation and Addition Reactions of 3-Oxoquinoxaline-2-carboxylates

      Satoru Miyamaru, Kazuto Umezu, Akinori Ito and Makoto Shimizu

      Article first published online: 7 APR 2015 | DOI: 10.1002/ejoc.201500225

      Thumbnail image of graphical abstract

      A one-pot synthesis of multisubstituted dihydroquinoxalin-2-ones using umpolung N-alkylation followed by oxidation and C-alkylation reaction is described. The synthesis of tricyclic compounds containing a dihydroquinoxaline skeleton was then carried out by ring closing metathesis (RCM) of N,C-bis-addition products containing olefins.

    6. α-Acyloxylation Reaction

      nBu4NI-Catalyzed α-Benzoxylation of Ketones with Terminal Aryl Alkenes

      Buddhadeb Mondal, Subas Chandra Sahoo and Subhas Chandra Pan

      Article first published online: 7 APR 2015 | DOI: 10.1002/ejoc.201500233

      Thumbnail image of graphical abstract

      An efficient synthesis for the α-benzoxylation of aryl ketones has been developed by using terminal aryl alkenes as the arylcarboxy surrogate. The products were obtained in moderate to good yields for a broad scope of substrates. Tetra-n-butylammonium iodide (TBAI) and tert-butyl hydroperoxide (TBHP) were employed as the catalyst and oxidant, respectively.

    7. Total Synthesis

      Total Synthesis of (±)-8-Oxo-erythrinine, (±)-8-Oxo-erythraline, and (±)-Clivonine

      Maomao He, Chunrong Qu, Bingbing Ding, Hao Chen, Yangyan Li, Guofu Qiu, Xianming Hu and Xuechuan Hong

      Article first published online: 7 APR 2015 | DOI: 10.1002/ejoc.201500265

      Thumbnail image of graphical abstract

      Total syntheses of the erythrina alkaloids (±)-8-oxo-erythrinine and (±)-8-oxo-erythraline have been developed, based on an intramolecular 6-exo-trig radical cyclization of a highly functionalized enamide (X = O, n = 1). An improved linear total synthesis of the amaryllidaceae alkaloid (±)-clivonine through a 6-endo-trig cyclization of a similar intermediate (X = O, n = 0) is also reported.

    8. Organocatalysis

      Copper(I)-Catalysed Domino Coupling and Cyclisation Reaction: A Mild, Expedient Route for the Synthesis of Indene and Dihydronaphthalene Derivatives

      Gullapalli Kumaraswamy and Guniganti Balakishan

      Article first published online: 7 APR 2015 | DOI: 10.1002/ejoc.201500284

      Thumbnail image of graphical abstract

      Bench-top CuI has been used as a catalyst to obtain a series of functionalised indene, dihydronaphthalene and cyclohexenone derivatives. Notably, the substrates were combined at a 1:1 ratio and no trace of fumarate or maleate side products were observed in spite of using diazo substrate and copper catalyst.

  20. Short Communications

    1. Smiles Rearrangement

      One-Pot Synthesis of N-Aryl-Nicotinamides and Diarylamines Based on a Tunable Smiles Rearrangement

      Shihui Liu, Shaofan Zhu, Ying Wu, Jiayu Gao, Pengfei Qian, Yanwei Hu, Linsen Shi, Shaohua Chen, Shilei Zhang and Yinan Zhang

      Article first published online: 7 APR 2015 | DOI: 10.1002/ejoc.201500222

      Thumbnail image of graphical abstract

      A substituent-mediated Smiles rearrangement to N-aryl-nicotinamides and diarylamines has been developed. In addition to the wide range of heterocyclic building blocks, the one-pot process also provides an efficient access to an on-market fungicide, boscalid.

    2. Cyclotrimerizations

      Rhodium(III)-Catalyzed [2+2+2] Cyclotrimerization of Diynes with Maleic Anhydrides as Alkyne Equivalents

      Takanori Matsuda and Kentaro Suzuki

      Article first published online: 7 APR 2015 | DOI: 10.1002/ejoc.201500252

      Thumbnail image of graphical abstract

      Substituted maleic anhydrides act as alkyne equivalents in a rhodium(III)-catalyzed reaction with 1,6-diynes to achieve a formal [2+2+2] cyclotrimerization.

  21. Full Papers

    1. Heterocyclic Spiro Compounds

      Tandem Prins Strategy for the Synthesis of Spiropyrrolidine and Spiropiperidine Derivatives

      Basi V. Subba Reddy, Suresh Yarlagadda, C. Ravikumar Reddy, M. Rajashekhar Reddy, Balasubramanyan Sridhar, Dayaka Satyanarayana and Bharatam Jagadeesh

      Article first published online: 2 APR 2015 | DOI: 10.1002/ejoc.201500215

      Thumbnail image of graphical abstract

      Cascade reactions between a 3-[(3-methylbut-2-enylamino)methyl]but-3-en-1-ol derivative and aldehydes in the presence of TMSOTf at 0 °C afford the corresponding spiropyrrolidine derivatives in good yields. Similar cyclization of a 3-[(4-methylpent-3-enylamino)methyl]but-3-en-1-ol derivative and aldehydes provides the corresponding spiropiperidines.

    2. Propargylic Substitution

      Palladium-Catalyzed Nucleophilic Substitution of Propargylic Carbonates and Meldrum's Acid Derivatives

      Ilaria Ambrogio, Sandro Cacchi, Giancarlo Fabrizi, Antonella Goggiamani and Antonia Iazzetti

      Article first published online: 2 APR 2015 | DOI: 10.1002/ejoc.201500337

      Thumbnail image of graphical abstract

      Propargylic carbonates react with Meldrum's acid derivatives in the presence of Pd(OAc)2 and P(2-furyl)3 in THF at 80 °C to give propargylic substitution products.

  22. Short Communications

    1. Diamine Synthesis

      Direct Catalytic Asymmetric Mannich-Type Reaction of Benzyl Isocyanide: Stereoselective Synthesis of 1,2-Diarylethylenediamines

      Keiji Tamura, Naoya Kumagai and Masakatsu Shibasaki

      Article first published online: 2 APR 2015 | DOI: 10.1002/ejoc.201500336

      Thumbnail image of graphical abstract

      Enantioenriched 4,5-diarylimidazolines were directly accessed by catalytic asymmetric C–C bond-forming reaction of benzyl isocyanide and N-(thiophosphinoyl)aldimines. The imidazolines were readily transformed into enantioenriched 1,2-diarylethylenediamines.

  23. Full Papers

    1. Nitrogen Heterocycles

      Synthesis of Diazirine-Based Photoreactive Saccharin Derivatives for the Photoaffinity Labeling of Gustatory Receptors

      Lei Wang, Takuma Yoshida, Yasuyuki Muto, Yuta Murai, Zetryana Puteri Tachrim, Akiko Ishida, Shiori Nakagawa, Yasuko Sakihama, Yasuyuki Hashidoko, Katsuyoshi Masuda, Yasumaru Hatanaka and Makoto Hashimoto

      Article first published online: 1 APR 2015 | DOI: 10.1002/ejoc.201500184

      Thumbnail image of graphical abstract

      Saccharin is one of the most common artificial sweeteners. Synthesis of photoreactive saccharin derivatives that contain a (trifluoromethyl)diazirinyl moiety at the 5- or 6-position is reported. These saccharin derivatives could be applied for functional analysis of gustatory receptors.

  24. Short Communications

    1. Corroles

      Control of Oligomerization and Oxidation Steps in the Synthesis of Tris(pentafluorophenyl)corrole

      Carl Blumenfeld, Katherine J. Fisher, Lawrence M. Henling, Robert H. Grubbs, Harry B. Gray and Scott C. Virgil

      Article first published online: 1 APR 2015 | DOI: 10.1002/ejoc.201500276

      Thumbnail image of graphical abstract

      The mechanistic features of oligomerization and oxidative cyclization steps in the synthesis of tris(pentafluorophenyl)corrole (1) are presented. Analysis of isolated intermediates allowed for the identification of conditions for complete end-capping with pyrrole. Conditions were also optimized for the controlled oxidation to the desired corrole 1. An 84 % yield was achieved during oxidation of the isolated precursor 6 and a 17 % overall yield of 1 was achieved on scale.

    2. Single-Walled Carbon Nanotubes

      Synthesis of Robust Precursors for the Controlled Fabrication of (6,6), (8,8), (10,10), and (12,12) Armchair Single-Walled Carbon Nanotubes

      Andreas Mueller and Konstantin Yu. Amsharov

      Article first published online: 1 APR 2015 | DOI: 10.1002/ejoc.201500266

      Thumbnail image of graphical abstract

      We report four robust precursors for the rational synthesis of isomerically pure armchair single-walled carbon nanotubes (SWCNTs). The precursor structures are specially “programmed” for fabrication of ultrashort (6,6), (8,8), (10,10), and (12,12) singly capped nanotubes bearing three CNT segments, effective seeds for controlled growth of helicity-pure SWCNTs by metal-catalyzed epitaxial elongation.

  25. Full Papers

    1. Peptide Coupling

      EDC·HCl and Potassium Salts of Oxyma and Oxyma-B as Superior Coupling Cocktails for Peptide Synthesis

      Yahya E. Jad, Sherine N. Khattab, Beatriz G. de la Torre, Thavendran Govender, Hendrik G. Kruger, Ayman El-Faham and Fernando Albericio

      Article first published online: 31 MAR 2015 | DOI: 10.1002/ejoc.201500142

      Thumbnail image of graphical abstract

      We have shown that combinations of rather simple and green reagents, such as EDC·HCl and the potassium salt of OxymaPure or Oxyma-B, give unique results in terms of yield and low levels of racemization. We envisage a broad application of these reagents in solid-phase and solution synthesis, and especially in the preparation of peptide-based nanomaterials.

    2. Functionalization of Nanostructures

      Epoxidation of Multi-Walled Carbon Nanotubes by Organocatalytic Oxidation

      Cosimo Annese, Lucia D'Accolti, Valentina Armuzza, Tatiana Da Ros and Caterina Fusco

      Article first published online: 31 MAR 2015 | DOI: 10.1002/ejoc.201500107

      Thumbnail image of graphical abstract

      An efficient method for the epoxidation of multi-walled carbon nanotubes (MWCNTs) is proposed. It leads to the production of materials that can be easily further functionalized by nucleophiles. Complete chemical (TGA, FTIR, XPS, Raman) and morphological (TEM) characterization of the materials has revealed a high degree of functionalization.

    3. Synthetic methods

      Synthesis of Fluorine-Containing 3,3-Disubstituted Oxetanes and Alkylidene Oxetanes

      Romain Laporte, Anais Prunier, Emmanuel Pfund, Vincent Roy, Luigi A. Agrofoglio and Thierry Lequeux

      Article first published online: 30 MAR 2015 | DOI: 10.1002/ejoc.201500172

      Thumbnail image of graphical abstract

      Access to fluoroalkylidene-oxetanes and -azetidines was realized from four-membered cyclic ketones and fluorosulfones.

    4. Cross-Coupling

      RhI-Catalyzed Site-Selective Decarbonylative Alkenylation and Arylation of Quinolones under Chelation Assistance

      Soonhyung Kwon, Dahye Kang and Sungwoo Hong

      Article first published online: 30 MAR 2015 | DOI: 10.1002/ejoc.201500187

      Thumbnail image of graphical abstract

      The C-2 selective alkenylation and arylation reactions of 4-quinolones were achieved by using a RhI-catalyzed decarbonylative coupling strategy to afford valuable C-2 functionalized 4-quinolones. The present method was compatible with a broad scope of substrates and applied to the C-3 selective functionalization of an isoquinolone scaffold.

  26. Microreviews

    1. C–H Activation

      Ubiquitous Benzoquinones, Multitalented Compounds for Palladium-Catalyzed Oxidative Reactions

      Alexandre Vasseur, Jacques Muzart and Jean Le Bras

      Article first published online: 30 MAR 2015 | DOI: 10.1002/ejoc.201500080

      Thumbnail image of graphical abstract

      This review highlights the multifaceted properties of benzoquinone when it is involved in PdII-catalyzed oxidative reactions and presents mechanisms proposed in the literature.

  27. Full Papers

    1. Diastereoselective Mannich Reactions

      Synthesis of Chiral β-Aminomalonates from 2-Chlorotetrafluoroethanesulfinyl Aldimines through the Mannich Reaction

      Kai Yang, Min Jiang and Jin-Tao Liu

      Article first published online: 30 MAR 2015 | DOI: 10.1002/ejoc.201500134

      Thumbnail image of graphical abstract

      An efficient method for the synthesis of chiral β-aminomalonates in good yields and with high diastereoselectivities was achieved through Mannich reactions between 2-chlorotetrafluoroethanesulfinyl aldimines and dialkyl malonates in the presence of N-trimethylsilylimidazole.

    2. Expanded Porphyrins

      Multi-Expanded Porphyrin Assemblies on Cyclophosphazene Scaffolds

      Tejinder Kaur, Tamanna K. Khan and Mangalampalli Ravikanth

      Article first published online: 30 MAR 2015 | DOI: 10.1002/ejoc.201500131

      Thumbnail image of graphical abstract

      Hexasapphyrin and octasapphyrin assemblies on cyclophosphazene scaffolds were synthesized in decent yields, and their molecular structures were elucidated by 1D and 2D NMR spectroscopy.

    3. Auxiliary-Mediated Ligation

      A Photocleavable Auxiliary for Extended Native Chemical Ligation

      Christina Nadler, André Nadler, Christine Hansen and Ulf Diederichsen

      Article first published online: 30 MAR 2015 | DOI: 10.1002/ejoc.201500033

      Thumbnail image of graphical abstract

      A UV-labile auxiliary for cysteine-free peptide ligation reactions was developed. This auxiliary, which is easily prepared, can be readily attached to a variety of N-terminal amino acids to facilitate ligation reactions at various junctions, and its cleavage efficiently proceeds through a mild photolysis reaction. This new auxiliary provides an excellent alternative to existing ligation auxiliaries.

    4. Natural Products

      Armochaetoglobins K–R, Anti-HIV Pyrrole-Based Cytochalasans from Chaetomium globosum TW1-1

      Chunmei Chen, Hucheng Zhu, Jianping Wang, Jing Yang, Xiao-Nian Li, Jing Wang, Keliang Chen, Yanyan Wang, Zengwei Luo, Guangmin Yao, Yongbo Xue and Yonghui Zhang

      Article first published online: 30 MAR 2015 | DOI: 10.1002/ejoc.201403678

      Thumbnail image of graphical abstract

      Eight rare pyrrole-based cytochalasans, armochaetoglobins K–R, were isolated from the solid culture broth of the fungus Chaetomium globosum, first isolated from the arthropod Armadillidium vulgare. Among them, armochaetoglobins L–N, Q, and R showed significant anti-HIV activities, with EC50 values ranging from 0.25 to 0.55 µM, and selective index (SI) values ranging from 20.43 to 75.42.

    5. Fluorinated Compounds

      Difluoromethyl and Chlorofluoromethyl Sulfoximines: Synthesis and Evaluation as Electrophilic Perfluoroalkylating Reagents

      Bruce Pégot, Céline Urban, Aaron Bourne, Thanh Nghi Le, Sébastien Bouvet, Jérôme Marrot, Patrick Diter and Emmanuel Magnier

      Article first published online: 26 MAR 2015 | DOI: 10.1002/ejoc.201500201

      Thumbnail image of graphical abstract

      Bromodifluoromethyl and dichlorofluoromethyl sulfoximines are transformed into the Hu electrophilic difluoromethylating reagent, and into a new chlorofluoromethylating reagent, respectively.

    6. Cascade Synthesis of Pyrroles

      Synthesis of Polysubstituted Pyrroles from Activated Alkynes and N-Propargylamines through Base-Catalyzed Cascade Reaction

      Jianquan Weng, Yong Chen, Binjie Yue, Meng Xu and Hongwei Jin

      Article first published online: 26 MAR 2015 | DOI: 10.1002/ejoc.201500166

      Thumbnail image of graphical abstract

      An efficient method for the synthesis of polysubstituted pyrroles from activated alkynes and N-propargylamines has been developed. This cascade process represents an atom- and step-economical way to construct a range of polysubstituted pyrroles and involves base-catalyzed Michael addition/alkyne carbocyclization or Michael addition/aza-Claisen rearrangement/cyclization.

  28. Microreviews

    1. Azolylpurine Derivatives

      Synthesis and Applications of Azolylpurine and Azolylpurine Nucleoside Derivatives

      Irina Novosjolova, Ērika Bizdēna and Māris Turks

      Article first published online: 23 MAR 2015 | DOI: 10.1002/ejoc.201403527

      Thumbnail image of graphical abstract

      This microreview describes different approaches for the synthesis of C(2)-, C(6)-, C(8)-, N(7)-, and N(9)-azolyl-substituted purine and purine nucleoside derivatives. Different methodologies including SNAr, cyclization, and transition-metal-catalyzed cross-coupling reactions are reviewed. These derivatives are important due to their wide applications in medicinal and biological chemistry.

    2. Anion Receptors

      Recent Advancements in Calix[4]pyrrole-Based Anion-Receptor Chemistry

      Indrajit Saha, Jeong Tae Lee and Chang-Hee Lee

      Article first published online: 19 MAR 2015 | DOI: 10.1002/ejoc.201403701

      Thumbnail image of graphical abstract

      Synthetic developments and anion-binding properties of newly developed calix[4]pyrroles are extensively discussed and accomplishments to date are summarized. Specifically, the formation of supramolecular organic frameworks and the possibility of customizing nanoscale structures through noncovalent interactions such as hydrogen bonding, anion–π interactions, and Coulombic interaction are addressed.

    3. Natural Product Synthesis

      Progress in the Preparation of Jatrophane Diterpenes

      Uwe Rinner

      Article first published online: 19 MAR 2015 | DOI: 10.1002/ejoc.201403598

      Thumbnail image of graphical abstract

      Jatrophane diterpenes are fascinating natural products, obtained from species of the Euphorbiaceae plant family. The biosynthesis of Euphorbiaceae constituents as well as their biological properties are briefly outlined followed by a detailed discussion of syntheses and approaches to jatrophane diterpenes.

  29. Full Papers

    1. Natural Product Synthesis

      A Diels–Alder Approach to a Communesin Model: A/B-Cyclization Route

      Angelo Sanzone and Peter Somfai

      Article first published online: 17 MAR 2015 | DOI: 10.1002/ejoc.201500177

      Thumbnail image of graphical abstract

      Compound 3, a model system for communesin F, was approached by using a Diels–Alder reaction for the introduction of the vicinal quaternary stereocentres. All six rings were introduced, although it was not possible to achieve the required bis-aminal oxidation state.

    2. Natural Products

      Structure and Absolute Configuration of Auriculamide, a Natural Product from the Predatory Bacterium Herpetosiphon aurantiacus

      Sebastian Schieferdecker, Nicole Domin, Christine Hoffmeier, Donald A. Bryant, Martin Roth and Markus Nett

      Article first published online: 17 MAR 2015 | DOI: 10.1002/ejoc.201500181

      Thumbnail image of graphical abstract

      Chemical analysis of culture extracts from the predatory bacterium Herpetosiphon aurantiacus led to the discovery of the new natural product auriculamide, the structure of which was elucidated by MS and NMR analyses. The absolute configuration was determined, after hydrolysis, by chromatographic comparison with synthetic standards. A gene cluster for the biosynthesis of auriculamide is proposed.

  30. Microreviews

    1. Synthesis of Azaheterocycles

      Furan's Gambit: Electrophile-Attack-Triggered Sacrifice of Furan Rings for the Intramolecular Construction of Azaheterocycles

      Igor V. Trushkov, Maxim G. Uchuskin and Alexander V. Butin

      Article first published online: 3 FEB 2015 | DOI: 10.1002/ejoc.201403580

      Thumbnail image of graphical abstract

      Chemistry is like chess! A gambit is a chess opening in which a player sacrifices something to achieve something else. The concept of the gambit is also used in organic chemistry. This review deals with intramolecular transformations pertaining to the sacrifice of a furan ring for the production of a variety of nitrogen heterocycles.

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